Paul Smith's ambitions started with cycling. His father made him get a gig at a clothinig warehouse, and he would bike there — his dream was to be a professional cyclist. Unfortunately, a cycling accident put a kibosh on that, and the young Smith started designing menswear. Known for his quirky take on classic men's style, the iconic designer has gotten the admiration of numerous celebrities, including rapper Yasiin Bey, and earned him a knighthood in 2000.

New Yorkers know all about Ralph Lauren's struggle. From selling neckties to designing a full-on lifestyle collection, plenty of vintage Polo gear has a strong place in hip-hop history. Beyond the Wu-Tang affiliation of items like the Snow Beach Parka, many 'Lo heads like producer Just Blaze share a fond sense of nostalgia with the designer and brand. Ralph Lauren's talent lies in his ability to translate his taste to a variety of guys: the uber preppy dude (Rugby), the menswear nerd (Purple Label), the Americana fiend (RRL), and the streetwear fan (Denim & Supply). It's evident from his clothing empire that he's not a businessman, he's a business, man.

Edge: Ralph Lauren. Sure, Paul Smith's designs and collections are definitely more fashion-forward, but they don't embody English style as a whole. Ralph Lauren's numerous lines easily encompass the spectrum of American fashion.